Symmetrically substituted biphenyls exhibit axial chirality
Symmetrically substituted biphenyl derivatives, particularly those with bulky ortho-substituents that restrict rotation about the central C-C bond, frequently exhibit axial chirality (atropisomerism).
The retrieved papers discuss various axially chiral biphenyl systems, including symmetrically substituted derivatives like 2,2'-disubstituted biphenyls and 2,2'-biphenols, confirming that restricted rotation leads to axial chirality.
Christian Wolf, Detlev H. Hochmuth, Wilfried A. König, Christian Roussel. Influence of Substituents on the Rotational Energy Barrier of Axially Chiral Biphenyls, II. 1996. https://doi.org/10.1002/jlac.199619960310
Paper [0] investigates the rotational energy barriers of 2,2'-disubstituted and symmetrically substituted biphenyl derivatives (such as 2,2'-bis(trifluoromethyl)biphenyl and 2,2'-diisopropylbiphenyl), confirming their axially chiral nature.
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Pearce-Higgins R, Hogenhout LN, Docherty PJ, Whalley DM, Chuentragool P, Lee N, Lam NYS, McGuire TM, Valette D, Phipps RJ. An Enantioselective Suzuki-Miyaura Coupling To Form Axially Chiral Biphenols.. 2022. https://doi.org/10.1021/jacs.2c06529
Paper [2] discusses the prevalence and significance of axially chiral atropisomeric 2,2'-biphenols.
Jie J, Yang H, Zhao Y, Fu H. Development of diverse adjustable axially chiral biphenyl ligands and catalysts.. 2023. https://doi.org/10.1016/j.isci.2023.106344
Paper [7] describes the development and application of axially chiral [1,1'-biphenyl]-2,2'-diol ligands and catalysts.
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